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Chemistry

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Also known as: 132036-88-5, Ramosetron [inn], (1-methylindol-3-yl)-[(5r)-4,5,6,7-tetrahydro-3h-benzimidazol-5-yl]methanone, 7zro0sc54y, Chembl1643895, Ramosetron (inn)

Molecular Formula

C₁₇H₁₇N₃O

Molecular Weight

279.34 g/mol

InChI Key

NTHPAPBPFQJABD-LLVKDONJSA-N

FDA UNII

7ZRO0SC54Y

Ramosetron is a serotonin 5-HT3 receptor antagonist commonly employed to treat nausea and vomiting, in addition to certain diarrheal conditions. It is believed to have higher potency and longer antiemetic action than other 1st generation 5-HT3 antagonists such as ondansetron. Currently, ramosetron is only approved for use Japan and in certain Southeast Asian countries.

1 2D Structure

Ramosetron

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1-methylindol-3-yl)-[(5R)-4,5,6,7-tetrahydro-3H-benzimidazol-5-yl]methanone

2.1.2 InChI

InChI=1S/C17H17N3O/c1-20-9-13(12-4-2-3-5-16(12)20)17(21)11-6-7-14-15(8-11)19-10-18-14/h2-5,9-11H,6-8H2,1H3,(H,18,19)/t11-/m1/s1

2.1.3 InChI Key

NTHPAPBPFQJABD-LLVKDONJSA-N

2.1.4 Canonical SMILES

CN1C=C(C2=CC=CC=C21)C(=O)C3CCC4=C(C3)NC=N4

2.1.5 Isomeric SMILES

CN1C=C(C2=CC=CC=C21)C(=O)[C@@H]3CCC4=C(C3)NC=N4

2.2 Other Identifiers

2.2.1 UNII

7ZRO0SC54Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-((1-methyl-3-indolyl)carbonyl)-4,5,6,7-tetrahydro-1h-benzimidazol

2. Methanone, (1-methyl-1h-indol-3-yl)(4,5,6,7-tetrahydro-1h-benzimidazol-5-yl)-, Monohydrochloride, (r)-

3. Nasea

4. Ramosetron Hydrochloride

5. Ym 060

6. Ym-060

7. Ym060

2.3.2 Depositor-Supplied Synonyms

1. 132036-88-5

2. Ramosetron [inn]

3. (1-methylindol-3-yl)-[(5r)-4,5,6,7-tetrahydro-3h-benzimidazol-5-yl]methanone

4. 7zro0sc54y

5. Chembl1643895

6. Ramosetron (inn)

7. (r)-(1-methyl-1h-indol-3-yl)(4,5,6,7-tetrahydro-1h-benzo[d]imidazol-6-yl)methanone

8. Unii-7zro0sc54y

9. Nor-ym 060

10. Ramosetron [mi]

11. Ramosetron [who-dd]

12. Schembl16701

13. Gtpl2301

14. Dtxsid0043842

15. Chebi:135156

16. Zinc5116719

17. Bdbm50334454

18. (-)-(r)-1-methylindol-3-yl 4,5,6,7-tetrahydro-5-benzimidazolylketone

19. Akos015896003

20. Db09290

21. R-146

22. D08466

23. A806353

24. Ar-270/43507766

25. Q2979523

26. (-)-(r)-1-methylindol-3-yl-4,5,6,7-tetrahydro-5-benzimidazolyl Ketone

27. (-)-(r)-1-methylindol-3-yl-4,5,6,7-tetrahydro-5-benzimidazolyl Ketone.

28. (1-methyl-1h-indol-3-yl)(4,5,6,7-tetrahydro-1h-benzimidazol-6-yl)methanone

29. (1-methylindol-3-yl)-[(5r)-4,5,6,7-tetrahydro-3h-benzimidazol-5-yl]methanone.

30. (r)-(-)-5-[(1-methyl-3-indolyl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole

31. (r)-5-[(1-methylindole-3-yl)carbonyl]-4,5,6,7-tetrahydro-1h-bezimidazole

32. Methanone, (1-methyl-1h-indol-3-yl)[(6r)-4,5,6,7-tetrahydro-1h-benzimidazol-6-yl]-

33. Methanone,(1-methyl-1h-indol-3-yl)[(6r)-4,5,6,7-tetrahydro-1h-benzimidazol-6-yl]-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₇N₃O
Molecular Weight	279.34 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	279.137162174 g/mol
Monoisotopic Mass	279.137162174 g/mol
Topological Polar Surface Area	50.7 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	413
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of nausea and vomiting and diarrhea-predominant irritable bowel syndrome in males.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Serotonin Antagonists

Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS. (See all compounds classified as Serotonin Antagonists.)

Antiemetics

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)

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